Bet Stories

65,713 results
Orientation
Length
Source
Infinite Scroll

A Really Stupid Bet

by staciliv on Sep 13, 2017
Mature

"This is a really good bet," I thought to myself. Over and over and over, I kept repeating to myself, "This is a really good bet. This is a really good bet. This is..." Of course I was trying to convince myself I hadn't made a serious mistake in judgment. Here I was sitting next to a man I barely knew, dressed like a slut -- or more correctly, barely dresse...

The Big Bet

by Gaius8666 on Sep 11, 2017
Exhibitionist & Voyeur

Now that school is out and all of the college kids are back home for vacation, my thoughts often return to my own time in school and the memories always make me crack a smile. Anyone who has ever been in a fraternity or a sorority usually has at least ONE crazy story to tell and being at a bar after work the other night, and hearing my work friends "one up"...

A Woman's Wager

by andtheend on Sep 13, 2017
Transsexuals & Crossdressers

A man who lost a bet must dress as a woman and discovers he likes it. "Pardon me, Madam," said Ed trying to hustle his shopping cart down the aisle by a very large woman. With her carriage blocking one side of the aisle, she was hunched over a shelf with her big ass blocking the other side of the aisle. When the woman turned to move her carriage out of the...

Are There Men Like That - Marge Ch. 03

by PattyMarie on Sep 17, 2017
Loving Wives

Disclaimer: This is a fantasy. No one in their right mind should participate in the activities the characters in this story do. If you don't like cuckold stories don't read it. Chapter 3 Third Date Conclusion. "I was thinking, after two months, that I might just survive all this with my marriage intact. I mean it seemed as if it was all behind me when,...

Losing the Bet

by talkmedown44 on Sep 13, 2017
Loving Wives

"They stink at free throws!" That was the start of this adventure. Kind of unexpected to tell the truth. When our group gets together we often make silly bets with weird payouts. We're all generally too poor and cheap to make bets about cash, so we like to come up with dares or actions or sometimes even chores the loser has to do. One time I had to wash a b...

Dark Angel Comes to Town...Again #03

by SusanJillParker on Sep 16, 2017
NonHuman

Witches and wizards never die. They are here now and are here to stay. ...And so is Satan. Warlocks, Wizards, and Sorcerers #1, 2, and 3 Taking this naming of witches a step further, in the way that woman can be witches, men can be warlocks, wizards, and sorcerers. How else can one explain the explosive success of Simon Cowell, Ryan Seacrest, and Randy Ja...

Never Bet with your Heart Ch. 01

by monkeytail10103 on Sep 12, 2017
Loving Wives

My wife Jill and I moved from North Carolina to New York City after I got a promotion with the investment group I worked with. We hated to leave our home state but it was a good opportunity and since we were in our late 20's and didn't want to start a family for a few more years we thought it would be fun to live in the city for a couple years and hopefully...

Freeway Show

by showife on Sep 18, 2017
Exhibitionist & Voyeur

This is a story that is part reality and mostly fantasy, I hope that you enjoy it. * Not too long ago we were driving back after a visit with some friends a few hours drive away. As usual, to break up the monotony of driving, I was enjoying playing with my wife Sam's body while we were driving. She's gotten quite used to being partially nude while driving,...

Yankees vs. Mets

by thehumpman on Sep 14, 2017
Loving Wives

As a lifelong New York Mets fan I always looked forward to interleague play and when they face the cross town rivals the Yankees. I was invited to the house of a buddy who grew up to be a lifelong Yankee fan along with his wife Karen. I brought a twelve pack of beer and a bag of pretzels which Karen took into the kitchen, my buddy John was in the living ro...

Vegas Gambling

by Denver Couple on Sep 15, 2017
Exhibitionist & Voyeur

I often have to sit in wonder of how I was lucky enough to find a woman like Megan. She is quite a lady. Totally feminine and very pretty! A Southern Bell with only a hint of an accent. Long blonde hair cascading down her 5' 7" frame to the middle of her back. Strong and sleek, built like a powerful sports car! She carries herself with an air of confidence,...